Acetovanillone → 4-(3-Chloropropoxy)-3-methoxyacetophenone

HRID 1049060Notes

Reaction equation

HRID 1049060 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[O:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][CH2:22][Cl:23]>CN(C)C=O>[Cl:23][CH2:22][CH2:21][CH2:20][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 2214AcetovanilloneHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneYield 243.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 1-(4-hydroxy-3-methoxyphenyl)ethanone (600 g, 3.61 mol, Purchased from Shanghai Bangcheng Chemical Co., Ltd.) and anhydrous potassium carbonate (698 g, 5.055 mol) in 2500 mL of N,N-dimethylformamide was added drop-wise with an N,N-dimethylformamide solution of 1-bromo-3-chloropropane (795.9 g, 1.4 mol) while maintaining the temperature below 25° C. Then the resulted mixture was kept at 25° C. for 10 h. After completion of the reaction, the precipitate was filtered and the filter cake was washed by a small amount of N,N-dimethylformamide. The filtrate was poured into ice water slowly with vigorous stirring. The precipitate was filtered, washed with water, and dried to give 827.2 g solid. Yield: 93.8%.

Workup

  1. temperaturewhile maintaining the temperature below 25° C
  2. customAfter completion of the reaction
  3. filtrationthe precipitate was filtered
  4. washthe filter cake was washed by a small amount of N,N-dimethylformamide
  5. additionThe filtrate was poured into ice water slowly with vigorous stirring
  6. filtrationThe precipitate was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-30f045a9660b408f9e98296447b28b8e
Source dataset
uspto-grants-2016_07
Patent number
US09382232B2

Reaction notes

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